A new synthetic approach to diastereomeric cyclopent-3-enylglycines, functionalized on the ring with a formyl group, and to cyclopentylglycine, substituted with a carboxy group, was devised by applying retro-aldol and retro-Claisen reactions, respectively, to diastereomeric 2-amino-3-ethoxycarbonyloxynorbornene-2-carboxylic acid derivatives and to diastereomeric 2-amino-3-oxo-norbornane-2-carboxylic acid derivatives. The goal of controlling the cis stereochemistry of the cyclopentyl substituents was reached . A partial control of the stereochemistry of the amino acidic carbon was achieved starting from 17 and using sodium hydrogen carbonate in acetone/DMF.
Chiral epimeric carboxycyclopentylglycines from norbornane derivatives: reaction conditions and ring strain effect on stereochemical control of amino acid centers / M.L. Gelmi, S. Pellegrino. ((Intervento presentato al convegno Chirality tenutosi a Parma nel 2005.
Chiral epimeric carboxycyclopentylglycines from norbornane derivatives: reaction conditions and ring strain effect on stereochemical control of amino acid centers
M.L. GelmiPrimo
;S. PellegrinoUltimo
2005
Abstract
A new synthetic approach to diastereomeric cyclopent-3-enylglycines, functionalized on the ring with a formyl group, and to cyclopentylglycine, substituted with a carboxy group, was devised by applying retro-aldol and retro-Claisen reactions, respectively, to diastereomeric 2-amino-3-ethoxycarbonyloxynorbornene-2-carboxylic acid derivatives and to diastereomeric 2-amino-3-oxo-norbornane-2-carboxylic acid derivatives. The goal of controlling the cis stereochemistry of the cyclopentyl substituents was reached . A partial control of the stereochemistry of the amino acidic carbon was achieved starting from 17 and using sodium hydrogen carbonate in acetone/DMF.Pubblicazioni consigliate
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